JP7457433B2 - Monomer composition with antibacterial function - Google Patents

Description

The subject disclosure relates to monomer(s) having antimicrobial functionality, and more particularly to monomer(s) containing one or more cationic and/or hydrophobic functional groups.

The discovery and improvement of antibiotics was one of the greatest achievements of the 20th century, revolutionizing medicine. For example, antibiotics such as penicillin, ciprofloxacin, and doxycycline achieve microbial selectivity by targeting and disrupting the metabolism of specific prokaryotes while remaining benign to eukaryotic cells. Can provide high selectivity. Proper administration can eradicate the infection. Unfortunately, this therapeutic specificity of antibiotics also results in counter-dosing, which allows for slight genetic variations due to underdosing (incomplete killing), thereby reducing the antibiotic's action. This is due to the development of resistance. Consequently, nosocomial infections caused by drug-resistant microorganisms, such as methicillin-resistant Staphylococcus aureus (MRSA), multidrug-resistant Pseudomonas aeruginosa, and vancomycin-resistant Enterococci (VRE) , is becoming more prevalent. Further complicating matters is the widespread use of antimicrobials in self-care products, disinfectants and hospital cleaning products, including anilides, bis-phenols, biguanides and quaternary ammonium compounds, where the main concern is , especially the development of cross-resistance and co-resistance with antibiotics used clinically in hospitals. Another unfortunate feature, for example with triclosan, is its cumulative and persistent action on the skin. Moreover, biofilms are associated with numerous nosocomial infections and transplant failures, and furthermore, eradication of biofilms remains an unmet task to date. An additional complication exists because antibiotics are unable to penetrate the extracellular polymeric material that encapsulates bacteria in biofilms, resulting in the development of drug resistance.

However, polymers with cationic charges can lead to electrostatic disruption of bacterial membrane interactions. Moreover, cationic polymers can easily be made amphiphilic by the addition of hydrophobic regions that allow for both membrane binding and integration or dissolution. Amphipathic balance has been shown to play an important role not only in antibacterial properties but also in hemolytic activity. Many such antimicrobial polymers exhibit relatively low selectivity as defined by relative toxicity to mammalian cells or hemolysis associated with pathogens.

The following presents a summary to provide a basic understanding of one or more embodiments of the invention. This summary is not intended to identify key or critical elements or to delineate any scope of particular embodiments or the claims. Its sole purpose is to present concepts in a simplified form as a prelude to the more detailed description that is presented later. One or more embodiments described herein describe methods and/or compositions related to ionenes with antimicrobial functionality.

In embodiments, a monomer is provided. The monomer may contain a single ionene unit. A single ionene unit may contain cations arranged along the molecular backbone. Also, hydrophobic functional groups can be covalently bonded to this molecular backbone, and single ionene units can have antimicrobial functionality.

In another embodiment, a monomer is provided. The monomer may contain a single ionene unit. A single ionene unit may include a cation arranged along a degradable molecular backbone, which may include a terephthalamide structure. Additionally, single ionene units may have antimicrobial functionality.

In another embodiment, a method is provided. The method can include dissolving an amine monomer and an electrophile in a solvent. The electrophile can be an alkyl halide. The method can also include forming a monomer from the amine monomer and the electrophile. The monomer can include a single ionene unit. The single ionene unit can include a cation disposed along the molecular backbone, and the single ionene unit can have antimicrobial functionality.

In another embodiment, a method is provided. The method may include dissolving the amine monomer and electrophile in a solvent. Amine monomers can include degradable molecular backbones, which can include terephthalamide structures. The method may also include forming a monomer from an amine monomer and an electrophile. The monomer may contain a single ionene unit. A single ionene unit may contain cations arranged along the degradable molecular backbone and may have antimicrobial function.

In another embodiment, a method is provided. The method may include contacting the pathogen with the monomer. Monomers may contain single ionene units, which may contain cations arranged along the molecular backbone. Additionally, hydrophobic functional groups may be covalently bonded to this molecular backbone. Additionally, single ionene units may have antimicrobial functionality. Additionally, this contact can electrostatically disrupt the pathogen's membrane.

FIG. 3 illustrates, by way of example, non-limiting ionene units, according to one or more embodiments described herein. FIG. 3 illustrates, by way of example, a non-limiting dissolution process that may be performed with one or more ionene units according to one or more embodiments described herein. 1 is a flowchart illustrating, by way of example, a non-limiting method that may facilitate production of one or more ionene compositions in accordance with one or more embodiments described herein. FIG. 1 illustrates, by way of example, non-limiting compound formation schemes that may facilitate the production of one or more ionene compositions according to one or more embodiments described herein. FIG. 2 illustrates, by way of example, a non-limiting ionene composition according to one or more embodiments described herein. FIG. 2 is another diagram illustrating, by way of example, a non-limiting ionene composition in accordance with one or more embodiments described herein. FIG. 3 illustrates, by way of example, a non-limiting chemical structural formula that may characterize one or more ionene units, according to one or more embodiments described herein. 1 is a flowchart illustrating, by way of example, a non-limiting method that may facilitate the production of one or more ionene units in accordance with one or more embodiments described herein. FIG. 2 illustrates, by way of example, a non-limiting compound formation scheme that may facilitate the production of one or more ionene compositions according to one or more embodiments described herein. FIG. 2 illustrates, by way of example, a non-limiting compound formation scheme that may facilitate the production of one or more ionene compositions according to one or more embodiments described herein. FIG. 3 illustrates, by way of example, a non-limiting table that may represent the antimicrobial functionality of various ionene compositions, according to one or more embodiments described herein. FIG. 2 is another diagram showing, by way of example, a non-limiting table that may represent the antimicrobial functionality of various ionene compositions according to one or more embodiments described herein. FIG. 3 is another diagram illustrating, by way of example, a non-limiting table that may represent the antimicrobial functionality of various ionene compositions, according to one or more embodiments described herein. FIG. 3 illustrates, by way of example, a non-limiting graph that may represent the hemolytic activity of various ionene compositions according to one or more embodiments described herein. FIG. 3 is another diagram illustrating, by way of example, a non-limiting graph that may represent the hemolytic activity of various ionene compositions in accordance with one or more embodiments described herein. FIG. 3 is another diagram illustrating, by way of example, a non-limiting graph that may represent the hemolytic activity of various ionene compositions in accordance with one or more embodiments described herein. FIG. 1 is a flow chart illustrating, by way of example, a non-limiting method that may facilitate killing of pathogens by one or more ionene units according to one or more embodiments described herein.

The following detailed description is illustrative only and is not intended to limit the embodiments or the application and/or uses of the embodiments. Furthermore, there is no intention to be bound by the wording or meaning of any information presented in the foregoing Background or Summary section or in the Detailed Description section.

One or more embodiments will now be described with reference to the drawings, in which like numerals are used to refer to like elements throughout. In the following description, for purposes of explanation, numerous specific details are set forth to provide a more thorough understanding of one or more embodiments. However, it will be apparent that in various instances, one or more embodiments may be practiced without such specific details.

The discovery and improvement of antibiotics was one of the greatest achievements of the 20th century, revolutionizing medicine. For example, antibiotics such as penicillin, ciprofloxacin, and doxycycline achieve microbial selectivity by targeting and disrupting the metabolism of specific prokaryotes while remaining benign to eukaryotic cells. Can provide high selectivity. Proper administration can eradicate the infection. Unfortunately, this therapeutic specificity of antibiotics also results in counter-dosing, which allows for slight genetic variations due to underdosing (incomplete killing), thereby reducing the antibiotic's action. This is due to the development of resistance. Consequently, nosocomial infections caused by drug-resistant microorganisms, such as methicillin-resistant Staphylococcus aureus (MRSA), multidrug-resistant Pseudomonas aeruginosa, and vancomycin-resistant Enterococci (VRE) , is becoming more prevalent. Further complicating matters is the widespread use of antimicrobials in self-care products, disinfectants and hospital cleaning products, including anilides, bis-phenols, biguanides and quaternary ammonium compounds, where the main concern is , especially the development of cross-resistance and co-resistance with antibiotics used clinically in hospitals. Another unfortunate feature, for example with triclosan, is its cumulative and persistent action on the skin. Moreover, biofilms are associated with numerous nosocomial infections and transplant failures, and furthermore, eradication of biofilms remains an unmet task to date. An additional complication exists because antibiotics are unable to penetrate the extracellular polymeric material that encapsulates bacteria in biofilms, resulting in the development of drug resistance.

However, polymers with cationic charges can lead to electrostatic disruption of bacterial membrane interactions. Moreover, cationic polymers can easily be made amphiphilic by the addition of hydrophobic regions that allow for both membrane binding and integration or dissolution. Amphipathic balance has been shown to play an important role not only in antibacterial properties but also in hemolytic activity. Many such antimicrobial polymers exhibit relatively low selectivity as defined by relative toxicity to mammalian cells or hemolysis associated with pathogens.

As used herein, the term "ionene" may refer to polymeric, copolymer, or monomeric units or combinations thereof that are arranged along or within the molecular backbone. or both, which may provide a positive charge. Examples of nitrogen cations include, but are not limited to, quaternary ammonium cations, protonated secondary amine cations, protonated tertiary amine cations, or imidazolium cations, or combinations thereof. Examples of link cations include, but are not limited to, quaternary phosphonium cations, protonated secondary phosphine cations, and protonated tertiary phosphine cations. As used herein, the term "molecular backbone" may refer to the central chain of covalently bonded atoms that form the primary structure of a molecule. In various embodiments described herein, side chains may be formed by attaching one or more functional groups to a molecular backbone. As used herein, the term "polyionene" may refer to a polymer that may contain multiple ionenes. For example, polyionenes may contain repeating ionene units.

FIG. 1 shows an exemplary diagram of a non-limiting ionene unit 100, according to one or more embodiments described herein. The ionene unit 100 may include a molecular skeleton 102, one or more cations 104, or one or more hydrophobic functional groups 106, or a combination thereof. In various embodiments, the ionene and/or polyionene described herein can include 100 ionene units. For example, the polyionenes described herein may include multiple ionenes bonded together, in which case the bonded ionenes may have a composition exemplified by 100 ionene units.

Molecular framework 102 may include a plurality of covalently bonded atoms (shown as circles in FIGS. 1 and 2). The atoms may be bonded in any desired configuration, including, but not limited to, chain configurations, or ring configurations, or combinations thereof. The molecular skeleton 102 includes one or more chemical structures, such as an alkyl structure, an aryl structure, an alkenyl structure, an aldehyde structure, an ester structure, a carboxy structure, a carbonyl structure, an amine structure, an amide structure, a phosphide structure, a phosphine structure, or any of these structures. may include, but are not limited to, combinations of, and others. Those skilled in the art will recognize that the number of atoms that may make up the molecular backbone may vary depending on the desired function of the ionene unit 100. For example, although nineteen atoms are shown in FIG. 1, molecular scaffolds 102 that can include tens, hundreds, or thousands of atoms, or combinations thereof, are also envisioned.

One or more cations 104 are located in the molecular backbone 102. As described above, the one or more cations 104 may include nitrogen or phosphorus cations or both. The cations 104 may be located along the molecular backbone 102 covalently bonded to other atoms in the molecular backbone 102. In various embodiments, the one or more cations 104 may comprise at least a portion of the molecular backbone 102. Those skilled in the art will recognize that the number of cations 104 that may comprise the ionene unit 100 may vary depending on the desired function of the ionene unit 100. For example, although two cations 104 are shown in FIG. 1, ionene units 100 that may include tens, hundreds, or thousands of cations 104, or combinations thereof, are also contemplated. Additionally, although FIG. 1 shows a plurality of equally spaced cations 104, other configurations in which the cations 104 are not equally spaced are also contemplated. Additionally, one or more cations 104 may be located at each end of the molecular backbone 102, or in an intermediate portion of the molecular backbone 102 between two or more ends of the molecular backbone 102, or both. The one or more cations 104 may provide a positive charge at one or more positions of the ionene unit 100.

One or more hydrophobic functional groups 106 may be attached to molecular backbone 102 to form side chains. One or more hydrophobic functional groups 106 may be attached to molecular framework 102 via a bond with cation 104. Additionally, one or more hydrophobic functional groups 106 may be bonded to electrically neutral atoms of molecular backbone 102. The ionene unit 100 is attached to one or more termini of the molecular scaffold 102, to all termini of the molecular scaffold 102, to an intermediate portion of the molecular scaffold 102 (e.g., a portion between two termini), or to a combination thereof. One or more hydrophobic functional groups 106 may be included.

Although FIG. 1 shows a biphenyl group as the hydrophobic functional group 106, other hydrophobic functional groups are also envisioned. Examples of hydrophobic functional groups 106 may include, but are not limited to, alkyl structures, aryl structures, alkenyl structures, ester structures, carboxy structures, carbonyl structures, carbonate structures, alcohol structures, or combinations thereof, or others. . In various embodiments, one or more hydrophobic functional groups 106 may include the same structure. In other embodiments, one or more hydrophobic functional groups 106 may include a first structure and one or more other hydrophobic functional groups 106 may include another structure.

FIG. 2 shows an example diagram of a non-limiting dissolution process 108 that may be facilitated by ionene units 100, according to one or more embodiments described herein. Repetition of similar elements utilized in other embodiments described herein is omitted for brevity. The lysis process 108 may include multiple stages, which collectively may include an attack mechanism that may be carried out by the ionene unit 100 against the pathogen cell. Examples of pathogen cells may include, but are not limited to, Gram-positive bacterial cells, Gram-negative bacterial cells, fungal cells, or yeast cells, or combinations thereof.

The target pathogen cell may include a membrane with a phospholipid bilayer 110. In various embodiments, the membrane can be an extracellular matrix. Phospholipid bilayer 110 may include multiple membrane molecules 112 covalently bound together, and membrane molecules 112 may include a hydrophilic head 114 and one or more hydrophobic tails 116. Additionally, one or more of the plurality of membrane molecules 112 may be negatively charged (indicated by the "-" symbol in FIG. 2).

At 118, an electrostatic interaction can occur between the positively charged cation 104 of the ionene unit 100 and one or more negatively charged membrane molecules 112. For example, the negative charge of one or more membrane molecules 112 can attract the ionene unit 100 to the membrane (e.g., phospholipid bilayer 110). The electrostatic interaction can also electrostatically disrupt the integrity of the membrane (e.g., phospholipid bilayer 110). Once the ionene unit 100 is attracted to the membrane (e.g., phospholipid bilayer 110), integration into the hydrophobic membrane can occur at 120. For example, at 120, one or more hydrophobic functional groups 106 of the ionene unit 100 can initiate integration into the phospholipid bilayer 110. The positively charged portion of the ionene unit 100 is attracted to and electrostatically disrupts one or more negatively charged membrane molecules 112 (e.g., one or more hydrophilic heads 114), while one or more hydrophobic functional groups 106 can penetrate between the hydrophilic heads 114 and enter the hydrophobic region created by the multiple hydrophobic tails 116.

Destabilization of the membrane (eg, phospholipid bilayer 110) may occur at 122 as a result of mechanisms occurring at 118 and/or 120. For example, the one or more hydrophobic functional groups 106 can act to cleave one or more negatively charged membrane molecules 112 from an adjacent membrane molecule 112 and positively charged ionenes. Unit 100 includes truncated membrane segments (e.g., one or more negatively charged membrane molecules 112 , or one or more neutral membrane molecules 112 , which constitute the layers of phospholipid bilayer 110 ). or both) may be moved away from adjacent segments of the membrane (eg, adjacent segments of phospholipid bilayer 110). As the cut segments of the membrane (e.g., phospholipid bilayer 110) are pulled apart, they become completely detached from other membrane molecules 112 at 124, thereby creating a gap in the membrane (e.g., phospholipid bilayer 110). can be formed. The gap formed may contribute to lysis of the target pathogen cells. In various embodiments, multiple ionene units 100 allow the lysis process 108 to be performed on the cells simultaneously. Moreover, the ionene units 100 involved in the dissolution process 108 do not need to undergo the same stages of the attack mechanism simultaneously.

FIG. 3 may facilitate the production of one or more ionene units 100 (e.g., which may be characterized by FIG. 1 or 2 or both) according to one or more embodiments described herein. 2 shows an example flow diagram of a non-limiting method 200. Repetition of similar elements utilized in other embodiments described herein is omitted for brevity. Method 200 may be performed using commercially available amine monomers and/or commercially available electrophiles to produce one or more ionene units 100. Ionene units 100 formed by method 200 may include one or more monomers.

Method 200 can include dissolving one or more amine monomers and one or more electrophiles in a solvent at 202. The amine monomer or monomers may contain one or more amino groups. Examples of amino groups that can constitute one or more amine monomers include primary amino groups, secondary amino groups, tertiary amino groups, heterocyclic groups (for example, imidazole groups or pyridine groups or both). ), or combinations thereof, or others. For example, one or more amine monomers can include a tertiary amino group. Additionally, when the one or more amine monomers include multiple amino groups, the first amino group of the amine monomer of interest may have the same or different structure as the second amino group of the amine monomer of interest. For example, one or more amine monomers can contain two or more tertiary amino groups. Additionally, the amine monomer or monomers may contain alkyl or aryl structures or both. Additionally, one or more amine monomers may include one or more functional groups (eg, hydroxy groups). Examples of amine monomers include 1-butylimidazole, N-methyldiethanolamine, bis[2-(N,N-dimethylamino)ethyl]ether, N,N,N',N'-tetramethyl-p-phenylenediamine. , N,N-dimethylbenzylamine, diethanolamine-derived compounds, or combinations thereof, or others.

The one or more electrophiles can include an alkyl halide (eg, a dialkyl halide). For example, one or more electrophiles can include bromide or chloride or both. Examples of electrophiles include p-xylylene dichloride, 4,4'-bis(chloromethyl)biphenyl, 1,4-bis(bromomethyl)benzene, 4,4'-bis(bromomethyl)biphenyl, 1,4 -Bis(iodomethyl)benzene, 1,6-dibromohexane, 1,8-dibromooctane, 1,12-dibromododecane, 1,6-dichlorohexane, 1,8-dichlorooctane, benzyl bromide, 3-chloro- 1-propanol, 1-bromohexane, 2-(2-chloroethoxy)ethanol, 3-chloro-1,2-propanediol, 1-bromooctane, 1-bromododecane, benzyl chloride, or combinations thereof, or others may include, but are not limited to.

The solvent can be an organic solvent. Additionally, the solvent can be a protic or aprotic solvent, or both, or an alcohol, or a combination thereof. Examples of solvents may include, but are not limited to, dimethylformamide (DMF), methanol, tetrahydrofuran (THF), dichloromethane (DCM), or combinations thereof, or others. To facilitate dissolution, the method 200 includes applying one or more amine monomers, one or more electrophiles, or a solvent, or a combination thereof, to a temperature of 15 degrees Celsius or more and 150 degrees Celsius or less. and stirring for a period of 8 hours or more and 72 hours or less (for example, 12 hours or more and 24 hours or less).

The method 200 includes forming at 204 one or more monomers from one or more amine monomers and/or one or more electrophiles, each monomer having 100 single ionene units. may include. One or more electrophiles may be covalently bonded to one or more amino groups of one or more amine monomers. For example, forming at 204 includes subjecting one or more amino groups of one or more amine monomers to alkylation and/or quaternization with one or more electrophiles. Therefore, one or more amino groups may be ionized by alkylation and/or quaternization. Thus, formation at 204 may simultaneously induce a polymer forming reaction (eg, formation of ionene unit 100) and charging (eg, formation of cation 104).

The single ionene unit(s) 100 constituting the one or more monomers may include one or more cations 104 (e.g., formed by ionization of one or more amino groups at 204) disposed along the molecular backbone 102. The one or more cations 104 may include protonated secondary amine cations, protonated tertiary amine cations, quaternary ammonium cations, or imidazolium cations, or combinations thereof. In addition, the single ionene unit(s) 100 constituting the one or more monomers may include one or more hydrophobic functional groups 106 covalently bonded to the molecular backbone 102 (e.g., via the one or more cations 104). For example, the one or more hydrophobic functional groups 106 may be derived from one or more electrophiles or formed by alkylation or quaternization or both at 204. The single ionene unit(s) 100, and thus the one or more monomers, formed at 204 may have antimicrobial functionality.

FIG. 4 illustrates one or more ionene compositions (e.g., characterized by FIGS. 1 and 2 or produced according to method 200 or Figure 2 shows an example non-limiting compound formation scheme that can facilitate the production of (which can be both). Repetition of similar elements utilized in other embodiments described herein is omitted for brevity. The compound formation scheme shown in FIG. 4 can be carried out using commercially available amine monomers and/or commercially available electrophiles to produce one or more ionene units 100. The ionene units 100 formed and produced by the compound formation scheme of FIG. 4 may constitute one or more monomers. Further, "n" in FIG. 4 may represent an integer of 1 to 1,000 (for example, an integer of 1 to 100). Further embodiments of the compound formation scheme shown in FIG. 4 while representing one or more specific amine monomers and/or electrophiles are also envisioned. For example, the primary mechanism of the compound formation scheme shown in FIG. (with reference to both) may be applied.

As shown in FIG. 4, scheme 300 includes a dialkyl halide (e.g., 4,4'-bis(chloromethyl)-1,1'-biphenyl) and a plurality of amine monomers (e.g., first amine monomer 306). may represent the formation of an ionene composition (e.g., first ionene composition 302) from. For example, a dialkyl halide (e.g., 4,4'-bis(chloromethyl)-1,1'-biphenyl) is combined with a plurality of amine monomers (e.g., first amine monomer 306) in a solvent (e.g., DMF). can be dissolved in The dialkyl halide (e.g., 4,4'-bis(chloromethyl)-1,1'-biphenyl), the plurality of amine monomers (e.g., first amine monomer 306), and the solvent are heated at a temperature of 15°C to 150°C. The mixture may be stirred at a temperature (eg, room temperature ("RT")) for 8 hours or more and 72 hours or less (eg, 12 hours or more and 24 hours or less).

In Scheme 300, a plurality of amine monomers (e.g., first amine monomer 306) are combined with an electrophile (e.g., 4,4'-bis(chloromethyl)-1,1'-biphenyl) and a plurality of amine monomers (e.g., first amine monomer 306). For example, it may be covalently bonded through one or more amino groups (eg, tertiary amino groups) of the first amine monomer 306). For example, Scheme 300 shows how one or more amino groups (e.g., tertiary amino groups) can be isolated using an electrophile (e.g., 4,4'-bis(chloromethyl)-1,1'-biphenyl). and alkylating to form an ionene composition (eg, first ionene composition 302) that includes a plurality of cations 104 (eg, quaternary ammonium cations). Additionally, the ionene composition (e.g., first ionene composition 302) is derived from an electrophile (e.g., 4,4'-bis(chloromethyl)-1,1'-biphenyl) as a result of alkylation. may include one or more hydrophobic functional groups 106. Accordingly, an ionene composition (e.g., first ionene composition 302) that may be produced by scheme 300 may include various features described in connection with FIGS. 1-2 or in accordance with various features of method 200. or both.

As shown in FIG. 4, scheme 308 provides an ionene composition (e.g., a second ionene monomer 306) from an alkyl halide (e.g., 4-(chloromethyl)biphenyl) and an amine monomer (e.g., first amine monomer 306). may represent the formation of composition 310). For example, an alkyl halide (eg, 4-(chloromethyl)biphenyl) can be dissolved in a solvent (eg, DMF) with an amine monomer (eg, first amine monomer 306). The alkyl halide (e.g., 4-(chloromethyl)biphenyl), amine monomer (e.g., first amine monomer 306), and solvent are heated at a temperature of 15° C. to 150° C. (e.g., room temperature (“RT”)). , for a period of 8 hours or more and 72 hours or less (for example, 12 hours or more and 24 hours or less).

In Scheme 308, an amine monomer (e.g., first amine monomer 306) is combined with an electrophile (e.g., 4-(chloromethyl)biphenyl) and one or more of the amine monomers (e.g., first amine monomer 306). may be covalently bonded through an amino group (eg, a tertiary amino group). For example, Scheme 308 alkylates one or more amino groups (e.g., tertiary amino groups) with an electrophile (e.g., 4-(chloromethyl)biphenyl) to give cation 104 (e.g., (e.g., second ionene composition 310). Additionally, the ionene composition (e.g., second ionene composition 310) has one or more hydrophobic functionalities derived from the electrophile (e.g., 4-(chloromethyl)biphenyl) as a result of alkylation. Group 106 may be included. Accordingly, the ionene composition (e.g., second ionene composition 310) that may be produced according to scheme 308 may include various features described in connection with FIGS. or both.

As shown in Figure 4, Scheme 314 combines multiple alkyl halides (e.g., 4-(chloromethyl)biphenyl) and diamine monomers (e.g., N,N,N',N'-tetramethyl-p-phenylenediamine). ) may represent the formation of an ionene composition (eg, third ionene composition 316). For example, multiple alkyl halides (e.g., 4-(chloromethyl)biphenyl) can be combined with a diamine monomer (e.g., N,N,N',N'-tetramethyl-p-phenylenediamine) in a solvent (e.g., DMF). can be dissolved in The temperature of multiple alkyl halides (e.g., 4-(chloromethyl)biphenyl), diamine monomers (e.g., N,N,N',N'-tetramethyl-p-phenylenediamine), and the solvent is 15°C or higher and 150°C or lower. (eg, room temperature (“RT”)) for a period of 8 hours or more and 72 hours or less (eg, 12 hours or more and 24 hours or less).

In Scheme 314, multiple alkyl halides (e.g., 4-(chloromethyl)biphenyl) are combined with diamine monomers (e.g., N,N,N',N'-tetramethyl-p-phenylenediamine) and diamine monomers (e.g., , N,N,N',N'-tetramethyl-p-phenylenediamine). For example, Scheme 314 alkylates one or more amino groups (e.g., tertiary amino groups) with multiple electrophiles (e.g., 4-(chloromethyl)biphenyl) to form multiple cations. 104 (e.g., a quaternary ammonium cation). Additionally, the ionene composition (e.g., third ionene composition 316) has one or more hydrophobic compounds derived from the plurality of electrophiles (e.g., 4-(chloromethyl)biphenyl) as a result of alkylation. may include a functional group 106. Accordingly, the ionene composition (e.g., third ionene composition 316) that may be produced by scheme 314 may include various features described in connection with FIGS. 1-2 or in accordance with various features of method 200. or both.

FIG. 5 may include various features described with respect to FIGS. 1-2, or may be produced according to various features of method 200 and/or the compound formation scheme shown in FIG. 4, or both. 1 shows an exemplary diagram of a non-limiting ionene composition that may include 100 single ionene units. Repetition of similar elements utilized in other embodiments described herein is omitted for brevity. The ionene composition shown in FIG. 5 may be monomeric and may have antimicrobial functionality.

For example, FIG. 5 shows a fourth ionene composition 402, a fifth ionene composition 404, a sixth ionene composition 406, a seventh ionene composition 408, an eighth ionene composition 410, a ninth ionene composition Composition 412, tenth ionene composition 414, twelfth ionene composition 418, thirteenth ionene composition 420, or fourteenth ionene composition 422, or combinations thereof may be shown. Each of the ionene compositions shown in FIG. 5 may be produced according to various features of method 200. Additionally, each of the ionene compositions shown in FIG. 5 can be produced according to the primary mechanism shown in the multiple compound formation scheme of FIG.

6 may include various features described with respect to FIGS. 1-2, or may be produced according to various features of method 200 and/or the compound formation scheme shown in FIG. 4, or both. 1 shows another exemplary non-limiting ionene composition that may include 100 single ionene units obtained. Repetition of similar elements utilized in other embodiments described herein is omitted for brevity. The ionene composition shown in FIG. 6 may be monomeric and may have antimicrobial functionality.

For example, FIG. 6 shows a fifteenth ionene composition 502, a sixteenth ionene composition 504, a seventeenth ionene composition 506, an eighteenth ionene composition 508, a nineteenth ionene composition 510, and a twentieth ionene composition. composition 512, the 21st ionene composition 514, the 22nd ionene composition 516, the 23rd ionene composition 518, the 24th ionene composition 520, or the 25th ionene composition 522, or a combination thereof. can be shown. Each of the ionene compositions shown in FIG. 6 may be produced according to various features of method 200. Additionally, each of the ionene compositions shown in FIG. 6 can be produced according to the primary mechanism shown in the multiple compound formation scheme of FIG.

FIG. 7 shows an exemplary diagram of a non-limiting chemical structure 600 that may characterize the structure of an ionene unit 100 according to one or more embodiments described herein. Repetition of similar elements utilized in other embodiments described herein is omitted for brevity. In various embodiments, one or more ionene units 100 characterized by chemical structure 600 can include a monomer composition.

As shown in FIG. 7, one or more ionene units 100 characterized by chemical structure 600 may include a degradable molecular skeleton 102. Additionally, degradable molecular scaffold 102 may include one or more terephthalamide structures. In various embodiments, one or more ionene units 100 characterized by chemical structure 600 may be derived from polyethylene terephthalate (PET), in which case one or more terephthalamide structures are present in the PET. It can be derived from However, one or more embodiments of chemical structure 600 may include a terephthalamide structure derived from one or more molecules other than PET.

“X” in FIG. 7 may represent one or more cations 104. For example, "X" is one or more cations selected from the group that may include, but is not limited to, one or more nitrogen cations, one or more phosphorus cations, and/or combinations thereof. 104. For example, "X" may include, but is not limited to, one or more protonated secondary amine cations, one or more protonated tertiary amine cations, one or more quaternary ammonium cations, or one or more nitrogen cations selected from the group which may include one or more imidazolium cations, or combinations thereof. In other cases, "X" includes, but is not limited to, one or more protonated secondary phosphine cations, one or more protonated tertiary phosphine cations, or one or more quaternary phosphine cations. may represent one or more link cations selected from the group which may include class phosphonium cations, or combinations thereof.

One or more cations 104 (eg, represented by “X” in chemical structure 600) may be covalently bonded to one or more linking groups to form at least a portion of the degradable molecular scaffold 102. One or more linking groups may link one or more cations 104 to one or more terephthalamide structures, thereby including molecular backbone 102. "Y" in FIG. 7 may represent one or more linking groups. The one or more linking groups can include any structure depending on the various characteristics of the molecular scaffold 102 described herein. For example, the linking group or groups can have any structure desired, including, but not limited to, a chain structure, or a ring structure, or a combination thereof. The one or more linking groups may include one or more linking groups including, but not limited to, alkyl structures, aryl structures, alkenyl structures, aldehyde structures, ester structures, carboxy structures, carbonyl structures, or combinations thereof, or the like. may include chemical structures. For example, "Y" can represent one or more linking groups that can include an alkyl chain having from 2 to 15 carbon atoms.

As shown in FIG. 7, in various embodiments, the one or more ionene units 100 characterized by the chemical structure 600 include a cation 104 (e.g., "X") at multiple positions along the molecular backbone 102. may include). For example, cation 104 can be located at either end of molecular backbone 102 (eg, as shown in FIG. 7). However, in one or more embodiments of chemical structure 600, molecular scaffold 102 may include fewer or more cations 104 than the two shown in FIG.

Additionally, "R" shown in FIG. 7 can represent one or more hydrophobic functional groups 106, according to various embodiments described herein. For example, one or more hydrophobic functional groups 106 can include one or more alkyl groups, or one or more aryl groups, or both. For example, hydrophobic functional group 106 can be derived from an alkyl halide. One or more hydrophobic functional groups 106 (e.g., represented as "R" in FIG. 7) may be attached to one or more of cations 104 (e.g., represented as "X" in FIG. 7) and/or molecular backbone 102. can be covalently bonded to one or more cations 104 (e.g., represented as "X" in FIG. 7), one or more linking groups (e.g., represented as "Y" in FIG. 7) , or one or more terephthalamide structures, or combinations thereof.

FIG. 8 depicts another exemplary flowchart of a non-limiting method 700 that may facilitate the production of one or more ionene units 100, characterized by chemical structure 600. Repetition of similar elements utilized in other embodiments described herein is omitted for brevity. The one or more ionene units 100 produced by method 700 may include a monomer composition and/or have antimicrobial functionality.

Method 700 can include dissolving one or more amine monomers in a solvent with one or more electrophiles at 702. The one or more amine monomers can include a degradable molecular backbone 102, which can include one or more terephthalamide structures. Additionally, amine monomers may contain one or more amino groups. For example, the amine monomer or monomers can be a tetraamine. Examples of amino groups that can constitute one or more amine monomers include primary amino groups, secondary amino groups, tertiary amino groups, heterocyclic groups (for example, imidazole groups or pyridine groups or both). ), or combinations thereof, or others. Additionally, if the one or more amine monomers include multiple amino groups, the first amino group of the amine monomer of interest may have the same or different structure as the second amino group of the amine monomer of interest.

The one or more electrophiles may include, for example, one or more alkyl halides (e.g., dialkyl halides). For example, the one or more electrophiles may include chlorides or bromides or both. Examples of electrophiles may include, but are not limited to, benzyl chloride, 3-chloro-1-propanol, 1-bromohexane, 2-(2-chloroethoxy)ethanol, 3-chloro-1,2-propanediol, 1-bromooctane, 1-bromododecane, 4-(chloromethyl)biphenyl, 1-bromodecane, or combinations thereof, or others.

The solvent can be an organic solvent. Additionally, the solvent can be a protic or aprotic solvent, or both, or an alcohol, or a combination thereof. Examples of solvents may include, but are not limited to, dimethylformamide (DMF), methanol, tetrahydrofuran (THF), dichloromethane (DCM), or combinations thereof, or others. To facilitate dissolution, method 200 comprises injecting one or more amine monomers, one or more electrophiles, or a solvent, or a combination thereof, at a temperature of 15° C. or higher and 150° C. or lower for 8 hours. It may further include stirring for at least 72 hours (for example, at least 12 hours and at most 24 hours).

In one or more embodiments, one or more amine monomers may be prepared by aminolysis of PET. For example, PET can be depolymerized by one or more aminolysis reagents. The one or more aminolysis reagents can be diamines. The first amino group of the diamine may include, but is not limited to, a primary amino group and a secondary amino group. The second amino group of the diamine may also include, but is not limited to, a primary amino group, a secondary amino group, a tertiary amino group, or an imidazole group, or a combination thereof. For example, in one or more embodiments, the secondary amino group is a tertiary amino group and/or an imidazole group.

Scheme 1, presented below, demonstrates three non-limiting example degradable amine monomers that can be prepared by aminolysis of PET.

Preparation of multiple degradable amine monomers (eg, according to Scheme 1) can be carried out without the need for catalysts and/or solvents. Additionally, aminolysis of PET can be performed using an excess of aminolysis reagent (eg, a 4-fold excess of aminolysis reagent). Moreover, aminolysis can depolymerize PET at elevated temperatures. Upon cooling, the target degradable amine monomer can crystallize due to excess amounts of reagent and alcohol byproduct (eg, ethylene glycol). The degradable amine monomer can then be filtered, rinsed (eg, with ethyl acetate) and used without the need for further purification.

Although Scheme 1 depicts three example degradable amine monomers derived from PET, other degradable amine monomers that may be derived from PET are also envisioned. For example, PET can be depolymerized using aminolysis reagents other than the three depicted in Scheme 1. For example, a primary amino group and/or a secondary amino group that can provide a hydrogen atom to facilitate bonding to the terephthalamide structure, and a secondary amino group and/or imidazole group that can later become the cation 104. Any aminolysis reagent that has both can be polymerized with PET to prepare a degradable amine monomer for use in 402. Additionally, the PET-derived degradable amine monomers described herein can include one or more amine monomers that can be utilized in method 700.

Additionally, in one or more embodiments, one or more amine monomers used with method 700 may be derived from molecules other than PET. Excess amounts of other starting molecules can be polymerized and/or depolymerized to prepare one or more amine monomers (e.g., can have degradable backbones). , a terephthalamide structure, or a tetraamine, or a combination thereof), one skilled in the art can readily recognize that this can be utilized with method 700.

Method 700 optionally comprises treating the one or more amine monomers, one or more electrophiles, and the solvent at a temperature of 15° C. or higher and 150° C. or lower for 8 hours or more and 72 hours or less (e.g., 12 hours). It may include stirring for a period of at least 24 hours).

Method 700 can include forming one or more monomers at 704 from one or more amine monomers and one or more electrophiles. The monomer can include a single ionene unit 100 (e.g., characterized by chemical structure 600), which can include cations 104 arranged along a degradable molecular backbone 102. Molecular framework 102 can include a terephthalamide structure (eg, as shown in chemical structure 600). Additionally, the single ionene unit 100 formed at 704 may have antimicrobial functionality. In one or more embodiments, forming at 704 may be performed under nitrogen gas filling. Additionally, the formation at 704 can generate cations by alkylation and/or quaternization with one or more electrophiles. In various embodiments, the terephthalamide structure containing the precipitate can be derived from PET that has been depolymerized to prepare one or more amine monomers.

During formation in 704, the nitrogen and/or phosphorus atoms located on the degradable amine monomer may be subjected to alkylation and/or quaternization with one or more electrophiles. Often, this allows the formation at 704 to simultaneously perform the polymer formation reaction (e.g., formation of repeating ionene units 100) and charging (e.g., formation of cations 104, including nitrogen and/or phosphorus cations) without the need for a catalyst. It can be induced without Additionally, the one or more hydrophobic functional groups 106 may be derived from one or more electrophiles, as a result of alkylation and/or quaternization processes, or may be derived from the degradable molecular backbone 102 ( for example, via one or more cations 104), or both.

For example, the single ionene formed in 704 may include one or more embodiments of the ionene unit 100 and may be characterized by one or more embodiments of the chemical structure 600. For example, the single ionene unit 100 formed in 704 may include a degradable molecular backbone 102, which may include one or more cations 104 (e.g., represented by "X" in the chemical structure 600), one or more linking groups (e.g., represented by "Y" in the chemical structure 600), one or more terephthalamide structures (e.g., as shown in FIG. 7), or one or more hydrophobic functional groups 106 (e.g., represented by "R" in the chemical structure 600), or a combination thereof. The one or more cations 104 may be nitrogen cations (e.g., quaternary ammonium cations, or imidazolium cations, or a combination thereof) or phosphorus cations (e.g., quaternary phosphonium cations), or a combination thereof. The cations 104 may be linked to one or more terephthalamide structures via one or more linking groups (e.g., alkyl or aryl groups, or both). Additionally, the one or more cations 104 may be bonded to one or more hydrophobic functional groups 106.

The antimicrobial activity of the repeating ionene units 100 produced by method 700 may be independent of molecular weight. Thus, method 700 targets conditions that can eliminate molecular weights reached by diffusion-limiting mechanisms (e.g., polymer precipitation) to moderate molecular weights (e.g., molecular weights less than 10,000 grams per mole (g/mol)). 100, which may aid in the solubility of the one or more ionene units 100 in the aqueous medium.

9 shows an exemplary diagram of a non-limiting compound formation scheme that may facilitate the production of one or more ionene compositions (e.g., characterized by chemical formula 600 or produced according to method 700, or both) according to one or more embodiments described herein. Repeated descriptions of similar elements utilized in other embodiments described herein are omitted for the sake of brevity. The ionene units 100 formed and produced according to the compound formation scheme of FIG. 9 may constitute one or more monomers. While representing one or more specific amine monomers and/or electrophiles, further embodiments of the compound formation scheme shown in FIG. 9 are also envisioned. For example, the main mechanism of the compound formation scheme shown in FIG. 9 may be applied to any amine monomer and/or electrophile according to various features described herein (e.g., with reference to chemical formula 600 and/or method 700).

As shown in FIG. ionene compositions (e.g., 26th ionene composition 802, 27th ionene composition 806, 28th ionene composition 808, or the twenty-ninth ionene composition 810, or a combination thereof). For example, one or more alkyl halides (e.g., benzyl bromide, 3-chloro-1-propanol, 3-chloro-1,2-propanediol, or 1-bromohexane, or combinations thereof) It may be dissolved in a solvent (eg, DMF) with a monomer (eg, fourth amine monomer 804). one or more alkyl halides (e.g. benzyl bromide, 3-chloro-1-propanol, 3-chloro-1,2-propanediol, or 1-bromohexane, or combinations thereof), amine monomers (e.g. , fourth amine monomer 804) and the solvent at a temperature of 15° C. or more and 150° C. or less (e.g., room temperature (“RT”)) for a period of 8 hours or more and 72 hours or less (e.g., 12 hours or more and 24 hours or less). , can be stirred.

In the compound formation scheme of Figure 9, one or more alkyl halides, such as benzyl bromide, 3-chloro-1-propanol, 3-chloro-1,2-propanediol, or 1-bromohexane, may be covalently bonded to an amine monomer (e.g., fourth amine monomer 804) through one or more amino groups (e.g., imidazole groups) of the amine monomer (e.g., fourth amine monomer 804). For example, the compound formation scheme of FIG. - an ionene composition (e.g., the twenty-sixth ionene composition 802, comprising a plurality of cations 104 (e.g., an imidazolium cation), alkylated with propanediol, or 1-bromohexane, or a combination thereof); a twenty-seventh ionene composition 806, a twenty-eighth ionene composition 808, or a twenty-ninth ionene composition 810, or a combination thereof. Further, the ionene composition (e.g., the twenty-sixth ionene composition 802, the twenty-seventh ionene composition 806, the twenty-eighth ionene composition 808, or the twenty-ninth ionene composition 810, or combinations thereof) may be alkylated. as a result of one or more electrophiles (e.g., benzyl bromide, 3-chloro-1-propanol, 3-chloro-1,2-propanediol, or 1-bromohexane, or combinations thereof). may include one or more hydrophobic functional groups 106 derived from the hydrophobic functional groups 106. Accordingly, the ionene compositions (e.g., the twenty-sixth ionene composition 802, the twenty-seventh ionene composition 806, the twenty-eighth ionene composition 808, or the twenty-ninth ionene composition) that may be produced by the compound formation scheme of FIG. 810 or combinations thereof) may include various features described in connection with FIGS. 1-2 or chemical structure 600 or combinations thereof, or may be produced according to various features of method 700, or otherwise If not, it could be both.

FIG. 10 illustrates one or more ionene compositions (e.g., characterized by chemical structure 600 or produced according to method 700, according to one or more embodiments described herein). Figure 1 shows an exemplary non-limiting compound formation scheme that may facilitate the production of (or both). Repetition of similar elements utilized in other embodiments described herein is omitted for brevity. The ionene units 100 formed and produced by the compound formation scheme of FIG. 10 may constitute one or more monomers. Further embodiments of the compound formation scheme shown in FIG. 10 are also envisioned while representing one or more specific amine monomers and/or electrophiles. For example, the primary mechanism of the compound formation scheme shown in FIG. (with reference to both) may be applied.

As shown in Figure 10, the compound formation scheme includes one or more alkyl halides (e.g., 3-chloro-1,2-propanediol, 1-bromohexane, 1-bromooctane, 1-bromododecane, 3 -chloro-1-propanol, or benzyl bromide, or combinations thereof) and amine monomers (e.g., fifth amine monomer 904); ionene composition 908, a thirty-second ionene composition 912, a thirty-third ionene composition 916, a thirty-fourth ionene composition 920, or a thirty-fifth ionene composition 924, or combinations thereof). For example, one or more alkyl halides (e.g., 3-chloro-1,2-propanediol, 1-bromohexane, 1-bromooctane, 1-bromododecane, 3-chloro-1-propanol, or bromide) benzyl, or a combination thereof) can be dissolved in a solvent (eg, DMF) along with an amine monomer (eg, fifth amine monomer 904). one or more alkyl halides (e.g., 3-chloro-1,2-propanediol, 1-bromohexane, 1-bromooctane, 1-bromododecane, 3-chloro-1-propanol, or benzyl bromide, or combinations thereof), amine monomers (e.g., fifth amine monomer 904), or solvents, or combinations thereof, for 8 hours at a temperature of 15° C. to 150° C. (e.g., room temperature (“RT”)). Stirring may be performed for a period of not less than 72 hours (for example, not less than 12 hours and not more than 24 hours).

The compound formation scheme of FIG. - propanol, or benzyl bromide, or a combination thereof) with an amine monomer (e.g., fifth amine monomer 904) and one or more amino groups (e.g., , tertiary group). For example, the compound formation scheme of FIG. - quaternized with bromooctane, 1-bromododecane, 3-chloro-1-propanol, or benzyl bromide, or combinations thereof) to contain multiple cations 104 (e.g., quaternary ammonium cations) , an ionene composition (e.g., a 30th ionene composition 902, a 31st ionene composition 908, a 32nd ionene composition 912, a 33rd ionene composition 916, a 34th ionene composition 920, or a 35th ionene composition 920). ionene composition 924, or combinations thereof). Further, the ionene composition (e.g., the 30th ionene composition 902, the 31st ionene composition 908, the 32nd ionene composition 912, the 33rd ionene composition 916, the 34th ionene composition 920, or the 34th ionene composition 920), As a result of quaternization, the ionene compositions 924 of 35, or combinations thereof) may contain one or more electrophiles (e.g., 3-chloro-1,2-propanediol, 1-bromohexane, 1- bromooctane, 1-bromododecane, 3-chloro-1-propanol, or benzyl bromide, or combinations thereof). Accordingly, the ionene compositions (e.g., 30th ionene composition 902, 31st ionene composition 908, 32nd ionene composition 912, 33rd ionene composition 916) that may be produced by the compound formation scheme of FIG. , thirty-fourth ionene composition 920, or thirty-fifth ionene composition 924, or combinations thereof) may include various features described in connection with FIGS. 1-2 or chemical structure 600 or combinations thereof. or may be generated according to various features of method 700, or both.

FIG. 11 illustrates a non-limiting table 1000 that may represent the antimicrobial efficacy of one or more ionene compositions according to one or more embodiments described herein. Repetition of similar elements utilized in other embodiments described herein is omitted for brevity. The ionenes described herein (e.g., may include the various features described in connection with FIGS. 1-2 or produced according to one or more features of method 200 or the compound formation scheme of FIG. 4, or both) A plurality of ionene compositions were tested against a wide range of pathogens to demonstrate the antimicrobial activity of 100 ionene units (e.g., the ionene compositions depicted in FIGS. It was evaluated.

The first column 1002 of the table 1000 may represent the ionene composition being evaluated. The second column 1004 of the table 1000 shows the minimum inhibitory concentration (MIC) for Staphylococcus aureus ("SA") of the subject ionene compositions in micrograms per milliliter (μg/mL). The third column 1006 of the table 1000 shows the MIC of the subject ionene compositions for Escherichia coli ("EC") in μg/mL. The fourth column 1008 of the table 1000 shows the MIC of the subject ionene compositions for Pseudomonas aeruginosa ("PA") in μg/mL. The fifth column 1010 of the table 1000 shows the MIC for Candida albicans ("CA") of the subject ionene compositions in μg/mL. The sixth column 1012 of the table 1000 shows the hemolytic activity (" _HC50 ") for rat red blood cells of the subject ionene compositions in μg/mL.

FIG. 12 illustrates a non-limiting table 1100 that may represent the antimicrobial efficacy of one or more ionene compositions according to one or more embodiments described herein. Repetition of similar elements utilized in other embodiments described herein is omitted for brevity. The ionenes described herein (e.g., may include the various features described in connection with FIGS. 1-2 or produced according to one or more features of method 200 or the compound formation scheme of FIG. 4, or both) Multiple ionene compositions were evaluated against a wide range of pathogens to demonstrate the antimicrobial activity of 100 ionene units (e.g., the ionene composition depicted in FIG. did.

The first column 1102 of table 1100 shows the ionene composition being evaluated. The second column 1104 of the table 1100 shows the minimum inhibitory concentration (MIC) for Staphylococcus aureus (“SA”) of the subject ionene compositions in micrograms per milliliter (μg/mL). The third column 1106 of the table 1100 shows the MIC of the subject ionene compositions for Escherichia coli ("EC") in μg/mL. The fourth column 1108 of table 1100 shows the MIC of the subject ionene compositions for Pseudomonas aeruginosa (PA) in μg/mL. The fifth column 1110 of the table 1100 shows the MIC for Candida albicans ("CA") of the subject ionene compositions in μg/mL. The sixth column 1112 of the table 1100 shows the hemolytic activity (" _HC50 ") for rat red blood cells of the subject ionene compositions in μg/mL.

13 illustrates a non-limiting table 1200 that may represent the antimicrobial efficacy of one or more ionene compositions according to one or more embodiments described herein. Repetition of similar elements utilized in other embodiments described herein is omitted for brevity. To demonstrate the antimicrobial activity of the ionenes described herein (e.g., ionene units 100, which may include various features of chemical formula 600 or may otherwise be produced according to one or more features of method 700, or the compound formation schemes of Figures 9 or 10, or both), multiple ionene compositions were evaluated against a wide range of pathogens.

The first column 1202 of table 1200 lists the ionene compositions being evaluated. The second column 1204 of table 1200 lists the minimum inhibitory concentration (MIC) in micrograms per milliliter (μg/mL) of the ionene compositions being evaluated for Staphylococcus aureus ("SA"). The third column 1206 of table 1200 lists the MIC in μg/mL of the ionene compositions being evaluated for Escherichia coli ("EC"). The fourth column 1208 of table 1200 lists the MIC in μg/mL of the ionene compositions being evaluated for Pseudomonas aeruginosa ("PA"). The fifth column 1210 of table 1200 lists the MIC in μg/mL of the ionene compositions being evaluated for Candida albicans ("CA"). The sixth column 1212 of table 1200 lists the hemolytic activity ("HC ₅₀ ") for rat red blood cells in μg/mL of the subject ionene compositions.

Figure 14 illustrates a non-limiting graph 1300 that may represent the hemolytic activity of various ionene compositions at various concentrations according to one or more embodiments described herein. Repeated descriptions of similar elements utilized in other embodiments described herein are omitted for brevity. For example, Figure 14 shows the hemolytic activity of various ionene compositions at concentrations ranging from 8 parts per million (ppm) to 2000 ppm. The hemolytic activity depicted in graph 1300 may relate to rat red blood cells.

The first line 1302 of the graph 1300 may represent the twenty-fifth ionene composition 522. The second broken line 1304 of the graph 1300 may represent the twenty-fourth ionene composition 520. Third fold line 1306 may represent third ionene composition 316. The fourth line 1308 of the graph 1300 may represent the eighteenth ionene composition 508. A fifth broken line 1310 of graph 1300 may represent a twenty-second ionene composition 516. A sixth broken line 1312 of graph 1300 may represent a twenty-third ionene composition 518. The seventh broken line 1314 of the graph 1300 may represent the seventeenth ionene composition 506. The seventh broken line 1316 of the graph 1300 may represent the twentieth ionene composition 512. The eighth broken line 1318 of the graph 1300 represents the 21st ionene composition 514, the 19th ionene composition 510, or the 16th ionene composition 504, or a combination thereof.

FIG. 15 illustrates a non-limiting graph 1320 that may represent hemolytic activity at various concentrations of various ionene compositions according to one or more embodiments described herein. Repetition of similar elements utilized in other embodiments described herein is omitted for brevity. For example, FIG. 15 shows the hemolytic activity of various ionene compositions at concentrations ranging from 8 parts per million (ppm) to 2000 ppm. The hemolytic activity depicted in graph 1320 relates to rat red blood cells.

The first broken line 1324 of the graph 1320 may represent the fourteenth ionene composition 422. The second broken line 1326 of the graph 1320 may represent the fourth ionene composition 402, the fifth ionene composition 404, the sixth ionene composition 406, the seventh ionene composition 408, the eighth ionene composition 410, the ninth ionene composition 412, the tenth ionene composition 414, the twelfth ionene composition 418, or the thirteenth ionene composition 420, or a combination thereof.

FIG. 16 illustrates a non-limiting graph 1400 that may represent hemolytic activity at various concentrations of various ionene compositions according to one or more embodiments described herein. Repetition of similar elements utilized in other embodiments described herein is omitted for brevity. For example, FIG. 16 shows the hemolytic activity of various ionene compositions at concentrations ranging from 8 parts per million (ppm) to 2000 ppm. The hemolytic activity depicted in graph 1400 may relate to rat red blood cells.

The first broken line 1402 of the graph 1400 may represent the thirty-third ionene composition 916. The second broken line 1404 of the graph 1400 represents the 26th ionene composition 802, the 27th ionene composition 806, the 28th ionene composition 808, the 29th ionene composition 810, the 30th ionene composition 902, It may represent a thirty-first ionene composition 908, a thirty-second ionene composition 912, a thirty-fourth ionene composition 920, or a thirty-fifth ionene composition 924, or a combination thereof.

Figure 17 shows another example flow diagram of a non-limiting method 1500 for killing pathogens, preventing pathogen growth, or preventing contamination by pathogens, or combinations thereof. Repetition of similar elements utilized in other embodiments described herein is omitted for the sake of brevity. Examples of pathogens include, but are not limited to, gram-negative bacteria, gram-positive bacteria, fungi, yeast, or combinations thereof, or others.

The method 1500 can include, at 1502, contacting a pathogen with one or more monomers that can include a single ionene unit 100. One or more single ionene units 100 may include one or more cations 104 arranged along the molecular backbone 102. One or more single ionene units 100 may also include one or more hydrophobic functional groups 106 covalently bonded (eg, via one or more cations 104) to molecular backbone 102. One or more cations 104 can be nitrogen cations or phosphorus cations or both. Examples of nitrogen cations may include, but are not limited to, protonated secondary amine cations, protonated tertiary amine cations, quaternary ammonium cations, or imidazolium cations, or combinations thereof. In one or more embodiments, molecular scaffold 102 may include one or more terephthalamide structures. The one or more monomers can include ionene compositions according to various embodiments described herein (eg, various features described with respect to FIGS. 1-10).

The method 1500 may include, at 1504, electrostatically disrupting a pathogen membrane when the pathogen is contacted with the monomer. The membrane may include a phospholipid bilayer 110. One or more cations 104 comprising the single ionene unit 100 may target and/or disrupt the pathogen membrane according to a lysis process 108. Additionally, the method 1500 may include destabilizing the pathogen membrane by integrating one or more hydrophobic functional groups 106 of the ionene unit 100 into the membrane.

Various structures (e.g., described with respect to FIGS. 1, 2, or 7, or combinations thereof), compositions (e.g., described with respect to FIGS. 4-6, 9-16), or methods described herein. (e.g., as described with respect to FIGS. 3, 8, or 17, or combinations thereof) or combinations thereof may be incorporated into a variety of applications. For example, this application can be applied to a variety of items such as, but not limited to, food packaging, medical equipment, floor surfaces, furniture surfaces, tools for wound healing (e.g., bandages and/or gauze), building surfaces, Plants (e.g. agricultural crops), ground, tillage equipment, beds, sheets, clothing, blankets, shoes, doors, door frames, walls, ceilings, mattresses, light fixtures, small surfaces, switches, sinks, handrails, remote controls, It may include vanities, computer equipment, carts, trolleys, large baskets, large containers, or combinations thereof, or other cleaning, disinfection, sterilization, or other processing, or combinations thereof. In another example, the application may include a medicament, a pharmaceutical salt, a hygiene product (eg, soap and/or shampoo), or a combination thereof, or the like. In a further example, the application may include agricultural sprays and/or aqueous solutions that may facilitate treatment of food crops.

Additionally, the term "or" is intended to mean an inclusive or rather than an exclusive or. That is, unless explicitly stated otherwise or clear from the context, "X utilizes A or B" is intended to mean either natural inclusive permutation. That is, if X utilizes A, X utilizes B, or X utilizes both A and B, then "X utilizes A or B" is defined as It is filled. Furthermore, as used in the subject specification and accompanying drawings, the terms "a" and "an" mean "one or more" and refer to the singular, unless explicitly stated otherwise or clear from the context. should generally be interpreted as covering As used herein, the terms "example" and/or "exemplary" are utilized to mean an example, instance, or exemplary act. For the avoidance of doubt, the subject matter disclosed herein is not limited by such examples. In addition, any aspect or design described herein as an "example" and/or "illustrative" is not necessarily to be construed as preferred or advantageous over other aspects or designs. Nor is it meant to exclude exemplary equivalent structures and techniques known to those skilled in the art.

What has been described above includes only examples of systems, compositions, and methods. Needless to say, it is not possible to describe every possible combination of reagents, products, solvents, or items for purposes of illustrating the present disclosure, but those skilled in the art will be able to understand the present disclosure. It can be appreciated that many further combinations and permutations are possible. Moreover, to the extent that the terms "comprising," "having," "having," and the like are used in the detailed description, claims, appendices, and drawings, such terms are used to define the claims. The term ``comprising'' is intended to be inclusive, as is the term ``comprising'' when used as a conversion word within the scope of the term. The description of various embodiments is presented for purposes of illustration and is not intended to be exhaustive or limiting to the disclosed embodiments. Many modifications and variations will be apparent to those skilled in the art without departing from the scope of the described embodiments. The terminology used herein is used to best describe the principles, practical implementation, or technical improvements of the embodiments over technology found in the marketplace, or to enable others of ordinary skill in the art to implement the disclosure herein. It was chosen to make it possible to understand the morphology.

Claims (7)

A monomer comprising a single ionene unit, the single ionene unit comprising a cation disposed along a molecular skeleton and a hydrophobic functional group covalently bonded to the molecular skeleton,
The monomer has a structure selected from the following group, and the single ionene unit has an antibacterial function.
In the above formula, n is an integer of 1 or more and 1000 or less. The monomer according to claim 1, wherein the hydrophobic functional group is derived from an alkyl halide. dissolving an amine monomer and an electrophile in a solvent; and
2. The method of producing a monomer according to claim 1 , wherein a monomer is formed from the amine monomer and the electrophile, the monomer comprising a single ionene unit;
A method comprising forming a monomer in which the single ionene unit includes cations arranged along the molecular backbone, wherein the single ionene unit has an antimicrobial function. The amine monomer has the following structure,
(In the above formula, n is an integer from 1 to 1000)
The electrophile is an alkyl halide selected from the following group:
(In the above formula, X is halogen)
The method according to claim 3. The method of claim 4, wherein the monomer is selected from the group consisting of:

(In the above formula, n is an integer of 1 to 1000.) 6. The method of claim 4 or 5, wherein said forming comprises quaternization to form a nitrogen cation, and said halogen is selected from the group consisting of bromine and chlorine. 7. The method of any one of claims 3 to 6, further comprising stirring the amine monomer, the electrophile, and the solvent at a temperature of at least 15 degrees Celsius (°C) and at most 150°C for a period of time of at least 12 hours and at most 24 hours.

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